(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 723303Notes

Reaction equation

HRID 723303 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C:13]([N:21]1[CH2:25][CH2:24][CH:23](O)[CH2:22]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:13]([N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

4

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 9920605HCID 9920605, compound

Product 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalYield 3%HCID 9668001-BENZOYLPYRROLIDINE

Procedure

It has been found that presence of 2–3% glucose in the reaction mixture increases the yield. As shown in table 7, 73% of N-benzoyl-3-hydroxypyrrolidine can be obtained by hydroxylation of N-benzoylpyrrolidine (2 mM) with 3.9 g/L of cells of HXN-200 in the presence of glucose (3%).

Workup

  1. temperatureincreases the yield

Sources & evidence

ORD record
ord-6ca740afb7ae4d8393dd5c085f1ffbf2
Source dataset
uspto-grants-2006_11
Patent number
US07141412B2

Reaction notes

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